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Firefly luciferin information


Firefly luciferin
Names
IUPAC name
(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
Other names
D-(−)-Luciferin, beetle luciferin
Identifiers
CAS Number
  • 2591-17-5
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4588411
  • 16735812 One of the other tautomeric representations
ECHA InfoCard 100.018.166 Edit this at Wikidata
EC Number
  • 219-981-3
PubChem CID
  • 92934
UNII
  • 5TBB02N29K
CompTox Dashboard (EPA)
  • DTXSID00894865 Edit this at Wikidata
InChI
  • InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1
    Key: BJGNCJDXODQBOB-SSDOTTSWSA-N
  • One of the other tautomeric representations: InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,13H,4H2,(H,15,16)/b10-9+/t7-/m1/s1
  • InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1
SMILES
  • O=C(O)[C@@H]1/N=C(\SC1)c2sc3cc(O)ccc3n2
Properties
Chemical formula
C11H8N2O3S2
Molar mass 280.32 g·mol−1
UV-vis (λmax) 330 nm (neutral and somewhat acidic aqueous solutions) [1]
Absorbance ε330 = 18.2 mM−1 cm−1 [1]
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Firefly luciferin (also known as beetle luciferin) is the luciferin, or light-emitting compound, used for the firefly (Lampyridae), railroad worm (Phengodidae), starworm (Rhagophthalmidae), and click-beetle (Pyrophorini) bioluminescent systems. It is the substrate of luciferase (EC 1.13.12.7), which is responsible for the characteristic yellow light emission from many firefly species.

As with all other luciferins, oxygen is required to elicit light; however, it has also been found adenosine triphosphate (ATP) and magnesium are required for light emission.[2][3]

  1. ^ a b "D-luciferin product information" (PDF). Sigma Aldrich.
  2. ^ McElroy WD (1947). "The Energy Source for Bioluminescence in an Isolated System". Proc Natl Acad Sci USA. 33 (11): 342–345. Bibcode:1947PNAS...33..342M. doi:10.1073/pnas.33.11.342. PMC 1079070. PMID 16588763.
  3. ^ Green A, McElroy WD (1956). "Function of adenosine triphosphate in the activation of luciferin". Arch Biochem Biophys. 64 (2): 257–271. doi:10.1016/0003-9861(56)90268-5. PMID 13363432.

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Firefly luciferin

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Firefly luciferin (also known as beetle luciferin) is the luciferin, or light-emitting compound, used for the firefly (Lampyridae), railroad worm (Phengodidae)...

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Luciferin

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them have arisen independently in the course of evolution. Firefly luciferin is the luciferin found in many Lampyridae species, such as P. pyralis. It is...

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Firefly luciferase

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enzyme catalyses the oxidation of firefly luciferin, requiring oxygen and ATP. Because of the requirement of ATP, firefly luciferases have been used extensively...

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Luciferase

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photoprotein. The name was first used by Raphaël Dubois who invented the words luciferin and luciferase, for the substrate and enzyme, respectively. Both words...

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Bioluminescence

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the species or group, e.g. firefly luciferin. In all characterized cases, the enzyme catalyzes the oxidation of the luciferin. In some species, the luciferase...

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Firefly

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light-emitting organs, usually on a female firefly's lower abdomen. The enzyme luciferase acts on luciferin, in the presence of magnesium ions, ATP, and...

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Osamu Shimomura

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[Structure of Sea Firefly Luciferin (Part 2–3) (Part 2) Properties and Molecular Formula of Sea Firefly Luciferin]. Chemical Journal of Japan...

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Vargulin

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Vargulin, also called Cypridinid luciferin, Cypridina luciferin, or Vargula luciferin, is the luciferin found in the ostracod Cypridina hilgendorfii, also...

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Chemiluminescence

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different for each species, they are given the generic name of luciferin. Firefly luciferin can be oxidized to produce an excited complex. Once it falls...

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Benzothiazole

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of its derivatives are found in commercial products or in nature. Firefly luciferin can be considered a derivative of benzothiazole. Benzothiazoles consist...

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Click chemistry

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1,2-aminothiol and a 2-cyanobenzothiazole to make luciferin, which is fluorescent. This luciferin fluorescence can be then quantified by spectrometry...

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Vargula hilgendorfii

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blue-coloured light by a specialized chemical reaction of the substrate luciferin and the enzyme luciferase. The luciferase enzyme consists of a 555-amino...

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Photinus pyralis

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Photinus pyralis, better known by the common name, the common eastern firefly, and colloquially called a "lightning bug", is a species of flying beetle...

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Mouse models of breast cancer metastasis

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metastasized. Ensembl genome database of model organisms Fate mapping Firefly luciferin Gene targeting Gene trapping Genetic recombination History of model...

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Firefly squid

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reactant luciferin and the necessary enzyme luciferase are located in a crystalline structure within rod-like bodies in their photophores. Firefly squid...

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List of enzymes

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Renilla-luciferin 2-monooxygenase EC 1.13.12.5 Cypridina-luciferin 2-monooxygenase EC 1.13.12.6 Firefly luciferase EC 1.13.12.7 Watasenia-luciferin 2-monooxygenase...

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Howard Harold Seliger

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Bioluminescence, Chemi-Luminescence and Enzyme Function in the Oxidation of Firefly Luciferin". Photochemistry and Photobiology. 10 (3): 153–170. doi:10.1111/j...

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Thiazoline

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contain thiazoline rings, one example being Firefly luciferin, the light-emitting molecule in fireflies. The amino acid cysteine is produced industrially...

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Pyrosequencing

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apyrase, and with the substrates adenosine 5´ phosphosulfate (APS) and luciferin. The addition of one of the four deoxynucleotide triphosphates (dNTPs)...

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Bioluminescent activated destruction

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cells in an organism, once they become cancerous, to create the firefly light source luciferin and luciferase to create light. The light itself would have...

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Bioluminescence imaging

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derived from the three groups above differ in key ways: Firefly luciferase requires D-luciferin to be injected into the subject prior to imaging. The peak...

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Photinini

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which contain it start to glow like the firefly when brought in contact with a luciferin-containing medium. Firefly luciferases differ slightly between taxa...

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Lampyris noctiluca

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regulating the oxygen flow to the light-producing membranes that contain luciferin. This light results from a chemical reaction facilitated by the enzyme...

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Arachnocampa luminosa

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protein that occurs in fireflies. However, the luciferin that the enzyme acts upon is entirely different to that of fireflies and, indeed, other currently...

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Omphalotus olearius

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called luciferase, acting upon a compound called luciferin, leading to the emission of light much as fireflies do when glowing. Unlike chanterelles, jack-o'-lantern...

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Photocyte

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photocytes in fireflies. A reaction among D-luciferin, luciferase, and ATP has been implicated in the mechanism of light production in firefly photocytes...

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Vargula tsujii

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plainfin midshipman fish (Porichthys notatus), as it is the source of luciferin for the bioluminescence seen in the fish. Goodheart, Jessica A.; Minsky...

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